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Bicyclo[2.1.1]hexan-2-one as a new probe for the study of π-facial selectivity in nucleophilic additions. A comment

✍ Scribed by Veejendra K. Yadav; K.Ganesh Babu; R. Balamurugan

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
111 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

The cation complexation model performs better than the hydride model and is at par with the transition state model at the HF/6-31G* and B3LYP/6-31G* levels. Electrostatic effects that rely on the residual charges on C5 and C6 of the title substrate and that are believed to contribute to the overall performance of the hydride model also perform poorly.

📜 SIMILAR VOLUMES

The bicyclo[2.1.1]hexan-2-one system: a
The bicyclo[2.1.1]hexan-2-one system: a new probe for the experimental and computational study of electronic effects in π-facial selectivity in nucleophilic additions
✍ Goverdhan Mehta; S.Robindro Singh; Vanessa Gagliardini; U.Deva Priyakumar; G.Nar 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 79 KB

The remotely substituted 5-exo-bicyclo[2.1.1]hexan-2-one system is introduced as a new probe to study long range electronic effects on p-face selectivity during hydride reduction and a systematic computational study demonstrates good predictability at the semi-empirical level.

On the origin of π-facial diastereoselec
On the origin of π-facial diastereoselectivity in nucleophilic additions to chiral carbonyl compounds. 2. Calculated transition state structures for the addition of nucleophiles to propionaldehyde 1, chloroacetyldehyde 2, and 2-chloropropionaldehyde 3.
✍ G Frenking; K.F Köhler; M.T Reetz 📂 Article 📅 1991 🏛 Elsevier Science 🌐 French ⚖ 773 KB

Summarv : The transition state structures for addition of LiH to 1, 2, and 3 are computed and analyzed at MP2/6-3lG(d)//HF/6\_3lG(d). Three factors are found to be important for the relative energies of the transition state structures: (i) the conformational energy of the aldehyde; (ii) the interac